7 Classic Cocktails Every Gentleman Should Know

Ditch that Red Bull and Vodka. It’s time to put on your big boy pants and start drinking real cocktails.

There comes a time in every man’s life when drinking becomes an art. It’s that shift from drinking anything to get drunk, to wanting to experience unique flavors, sights and scents.

This happens around the time a man realizes that quality is often more important than quantity. When he realizes college isn’t the end of his education. And that in order to be a real gentleman, he’ll have to keep learning and challenging himself. Start listening more than he talks. Learning from those around him and from past generations.

Men in the early 20th century knew how to drink. Cocktails essentially grew out of the need to cover up the nasty taste of liquor back then. When they drank whiskey, they weren’t getting “subtle hints of vanilla and caramel.” The hooch could be pretty rough. So, getting creative with cocktails wasn’t just the result of idle curiosity. It was a necessity.

What amazes me is how the classic cocktail recipes continue to stand the test of time. Just like the Stradivari’s and their violins, early “mixologists” somehow got it right from the getgo. Sure, we can create fancy derivations. But at the end of the day, it’s pretty hard to improve on greatness.

Here are some of the classic cocktails every man should know how to make:

Manhattan

Originally invented around the 1870s, the Manhattan is one of THE classic cocktails. Like many of those original drinks, it’s about tasting the liquor in its full glory. No hiding behind mixers here. But it’s not about brute force either. There’s some elegance to it, and that’s what makes it an amazing cocktail.

2 oz rye or bourbon

1/2 oz sweet vermouth

1-2 dashes bitters

Maraschino cherry or lemon twist for garnish

Combine the rye, vermouth and bitters in a mixing glass or shaker with ice. Stir for a bit, then strain into a chilled cocktail glass. Garnish with a cherry or lemon twist.

Martini

A couple things to clear up: (1) The original martini was made with gin. If you want vodka in it you need to order a “vodka martini.” (2) Even a dry martini should contain SOME vermouth, otherwise it’s just chilled gin. Although I’m still amused by the Winston Churchill dry martini: in his version he preferred to simply “observe the vermouth” from across the room while drinking his chilled gin. (Click here to watch my video on how to make a martini.) Here is the classic martini recipe:

2-1/2 oz gin

1/2 oz dry vermouth

Olives or a lemon twist for garnish

Pour gin and vermouth into a shaker or mixing glass filled with ice. Stir for a bit, then strain into a chilled cocktail glass. Garnish with olives or lemon twist.

Old Fashioned

This is my go-to. There’s something so hearty and simple about the Old Fashioned. If you’ve got bourbon or rye on hand and you’ve got bitters, essentially all you need is a little sweetness. Invented in the 19th century (hence the name), it’s rumored to have started as a breakfast drink. Hey, if the average life expectancy was only 43, you’d wash down your muesli with a little booze too! (Click to watch my video on how to make an Old Fashioned.

Optional: Cherry or orange slice for muddling, or lemon twist for garnish

Add the sugar or simple syrup to the bottom of a rocks glass. Add the bitters and a splash of soda. Muddle together the simple syrup, bitters and soda (and fruit if you’re using it) with a spoon or muddler. Add ice, and pour in the rye or bourbon, stirring it all together. Optional: rub the lemon twist around the brim of the glass to bring out the scent of the oils before dropping it in the glass.

Classic Daiquiri

Another favorite of mine. The classic daiquiri is not the 7-11 slushy you thought you knew. It’s anything but a girly drink. I like to say the daiquiri is the VW Bug of cocktails. It’s so easy to tinker with, you can see how people got carried away adding in all manner of fruit and flair.

2 oz rum

1 oz simple syrup

1 oz freshly squeezed lime juice

Lime wedge for garnish

Combine the rum, simple syrup and lime juice with ice in a shaker and shake vigorously. Strain into a cocktail glass or pour into a rocks glass with the ice. Add a lime wedge for garnish.

Sidecar

There’s something elegant about this classic cocktail that brings to mind smartly dressed chaps in top hats and white gloves. It is considered one of the classic “sours,” in the same family as the whiskey sour and the margarita. If this is the “sidecar,” I’m curious to know what the actual motorcycle tastes like. I’m guessing amazing.

2 oz brandy

1 oz Cointreau

1 oz freshly squeezed lemon juice

A bit of sugar for the rim (optional)

Optional: rub lemon juice on the rim of a cocktail glass and dip into some sugar. Combine brandy, Cointreau and lime juice in a shaker with ice and shake vigorously. Strain and pour into the chilled cocktail glass.

Margarita

A younger derivation of the sidecar, this is a great vehicle for good tequila but just as much so for some beautifully fresh citrus on a hot day. If all you’ve known until now is margaritas made with store-bought “margarita mix,” prepare to have your mind blown.

2 oz agave tequila

1 oz Cointreau

1 oz freshly squeezed lime juice

Lime wedge for garnish

A bit of salt for the brim (optional)

Optional: rub lime juice on the rim of the glass and dip into some salt. Combine tequila, Cointreau and lime juice in a shaker with ice and shake vigorously. Strain and serve in the chilled cocktail glass or into a rocks glass with the ice. Add a lime wedge for garnish.

Negroni

This is an acquired taste for some. The bitterness of the Campari can be a bit intense. But when made well, it is one of the best representations of “balance” in the cocktail world. The story goes that an Italian nobleman “Count Negroni” wanted a little extra kick in his Americano (a blend of Campari, sweet vermouth and soda). So the bartender substituted gin for the soda. And pretty soon everyone in the land wanted an Americano “the Negroni way.”

1-1/2 oz gin

1-1/2 oz Campari

1-1/2 oz sweet vermouth

Orange slice or lemon peel for garnish (optional)

Pour gin, Campari, and vermouth into a rocks glass with ice and stir well. Garnish with an orange slice or lemon peel.

I’d be curious to know what other classic cocktails you’ve been enjoying. What would you add to this list? Leave your thoughts in the comments section below.

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About Kyle Ingham

Kyle Ingham is the Founder and Editor of The Distilled Man, an online channel that helps everyday guys become well-rounded gentlemen. Kyle is a husband, new father, blogger, podcaster, and a recovering advertising executive. For the past 7 years, he's been helping men learn the essential skills and knowledge they need to become better, more confident men. Kyle enjoys Bourbon, burritos and the occasional pirate joke. He lives in the San Francisco Bay Area with his wife and son.

Reader Interactions

Comments

That’s a terrible way to make an old fashioned. Try just a splash of syrup or gum bitters, couple dashes of bitters, and bourbon or rye over a large ice cube. If it’s too strong for you add a little water or soda or just let that cube melt a bit. Don’t mess up this timeless drink with muddled fruit and sugar cubes and soda. Bleh.

Hey John, thanks for your comment. I agree about the muddled fruit–I prefer keeping it bare bones with simple syrup, or sugar if I’m too lazy. That’s why I listed the fruit as optional. I like the addition of a little splash of soda just for mouthfeel.

I like your list here although I would have taken out and added a few; it is still pretty nice either way you go. If you ever decide to update this list I would like to see you add a white Russian to the mix.

I love a good Manhattan and have found it to be a good base. We’ve taken that base and added things like Herbsaint gives it a Sazerac taste (a good sazerac is my favorite drink). It’s fun to play around with the basic recipie a bt

Thanks Brian, that’s a great point. Once you get the basic recipes down, you can “tinker” and find new combinations that you like. As I like to say: with cocktails, the journey is just as fun as the destination.

Great article. One can’t go wrong knowing these drinks. I would rather know these well then 100 half ass. As I delve into mixology and begin this journey I am noticing a certain level of snobbishness as I read some comments on here about how drinks “should” be made. It’s not rocket science and we should be having fun.

Thanks Robert! Yes, the sidecar is a terrific drink. And you can play around with substituting different liquors as well. Definitely agree with you on the Tom Collins, that’s a mighty tasty drink, especially on a hot day.

HI Kyle, I recently watched an old movie from the ’40’s. In the movie they were drinking champagne cocktails. I found a recipe and tried it; here’s how you make one: Take a champagne flout or an older version of that with a wider mouth to it, which I use. Drop one sugar cube in it which you soak with bitters. Fill with cold champagne and there you have it! You taste the champagne and the bitters as well as your drink turning a sort of rose or reddish color. Try it and see what you think?

HI Kyle, I am of Danish descent. The Danes drink acivit which is made from vodka with a taste of caraway seeds;l it is sort of an acquired taste. I will have to see if they mix drinks from it or just like it is. At Christmas time, they take a bottle of it, put it in container filled with water and set it outside to freeze. When they drink it, they bring the container in and pour it right out of the bottle that is still frozen in the container. Another Christmas drink is Klogg. That’s for another time. Gary